Methanol → 5-[2,4-Bis(benzyloxy)-5-chlorophenyl]-isoxazole-3-carboxylic acid

HRID 389934ノート

反応式

HRID 389934 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([C:29]([O:31]CC)=[O:30])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[Li+].[OH-]>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([C:29]([OH:31])=[O:30])[CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 24774040Ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate

生成物 1

HCID 670835065-[2,4-Bis(benzyloxy)-5-chlorophenyl]-isoxazole-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate (200 mg, 0.43 mmol), methanol (10 ml), water (6-7 ml), and LiOH (16 mg, 0.65 mmol) was allowed to stand at 50-60° C. for 24 h. The solution was concentrated under vacuo to remove methanol, and the remaining aqueous solution was extracted with Et2O to remove traces of unreacted starting material. The aqueous solution was acidified with 1 M HCl and extracted with three portions of AcOEt. The combined organic extracts were washed with saturated aqueous sodium chloride and dried over sodium sulfate. Removal of the solvent under reduced pressure afforded a residue, which was chromatographed on silica gel (DCM/methanol: 9/1).

後処理

  1. concentrationThe solution was concentrated under vacuo
  2. customto remove methanol
  3. extractionthe remaining aqueous solution was extracted with Et2O
  4. customto remove traces
  5. extractionextracted with three portions of AcOEt
  6. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent under reduced pressure
  9. customafforded a residue, which
  10. customwas chromatographed on silica gel (DCM/methanol: 9/1)

出典と根拠

ORDレコード
ord-bcc4e13204e74a96a6176b2e9e70084c
出典データセット
uspto-grants-2013_02
特許番号
US08383616B2

反応ノート

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